Photo-fluorodecarboxylation of 2-Aryloxy and 2-Aryl Carboxylic Acids

Photo-fluorodecarboxylation of 2-Aryloxy and 2-Aryl Carboxylic Acids

Coming to light: The title reaction simply requires an aqueous alkaline solution of Selectfluor and light. The method is inexpensive and effective for a wide range of neutral and electron‐poor 2‐aryloxy and 2‐aryl acetic acids to provide fluoromethyl ethers (see scheme) and benzyl fluorides, respect...

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Veröffentlicht in:Angewandte Chemie International Edition 2012-10, Vol.51 (43), p.10804-10807
Hauptverfasser: Leung, Joe C. T., Chatalova-Sazepin, Claire, West, Julian G., Rueda-Becerril, Montserrat, Paquin, Jean-François, Sammis, Glenn M.
Format: Artikel
Sprache:eng
Schlagworte:
Acetic acid
Aromatic compounds
Carboxylic acids
Carboxylic Acids - chemistry
Ethers
Ethers - chemistry
Excitation
Fluorides
Fluorides - chemistry
fluorine
Fluorometers
Free Radicals - chemistry
Light
photochemistry
radical reactions
reaction mechanisms
Sodium Hydroxide - chemistry
synthetic methods
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Beschreibung
Zusammenfassung:Coming to light: The title reaction simply requires an aqueous alkaline solution of Selectfluor and light. The method is inexpensive and effective for a wide range of neutral and electron‐poor 2‐aryloxy and 2‐aryl acetic acids to provide fluoromethyl ethers (see scheme) and benzyl fluorides, respectively. The mechanism most likely proceeds through an initial aryl excitation with a subsequent single‐electron transfer.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201206352